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"Upgrading" an extremely crufty, unstable Windows 3.1 installation on a 486 by ironing the buggy first edition of Windows 95 over it. (I didn't even think that many illegal operations were possible at once.)

Throwing away high-density floppies because they couldn't work in a 360k drive.

Tearing 5¼" floppy drives apart and throwing them away because they couldn't read disks...aligning or cleaning the heads never occurred to me.

Painting spare PC cards and turning them into art sculptures in boredom.

Finding a dumpster with IBM Model F keyboards tossed inside, and leaving them there instead of diving and taking them home.

Scaping a number of perfectly good ATs by disassembly and then folding the sheet metal parts till they fit in the bin. Same with various working IBM monitors - I would break off the CRT vacuum seal, reassemble it and and drop in the bin. No one wanted them at the time, only 12 years ago.

Tearing 5¼" floppy drives apart and throwing them away because they couldn't read disks...aligning or cleaning the heads never occurred to me

I'm guilty of this one. It was before I knew anything much about computer hardware years ago. I had a nice drive which just didn't seem to read my System 80 disks. Figuring it was toast I tossed it into the skip bin.

A few weeks later I discovered the reason many of my disks didn't work was because the media had become sticky and degraded. No doubt I had glugged up the drive heads trying to read them. The drive was probably perfectly ok...it just needed a good clean.

Taking apart a Northgate 286 because the power supply had failed and I wanted to see what hard disk platters looked like.

It was the last in a line of handmedown/garage sale "vintage" computers that my family bought for ~$80 each before my parents were convinced to buy our first "new" computer, a Cyrix 6x86 machine. The 286 had served us well for years and was the first PC we had with a hard drive, but the new machine was in place when it died and 12 year old me was curious what the inside of the hard drive looked like.

Thankfully I saved the machine that we had 2 machines before that, an IBM 5150 (the later 256k model) in all of the original boxes and with all the original manuals.....that was used as a demo machine at IBM's Burlington VT plant open house in ~1982. (lots of fun games on the IBM Open House demo floppy!)

- Taking apart my NEC 386 luggable laptop to upgrade the processor but postponing after finding the processor was a different size or socket than what I was intending (maybe I thought I could upgrade it to a 486 or something stupid). Sat on it too long, put it in a box then forgot how it went back together. Pretty sure I still have the box somewhere.
- A friend found an old Tandy desktop and tore it up for fun and ended up dragging the hard drive or something down the road.. literally. My like for vintage gear had just begun but they were so common at the time it wasn't of interest.
- Still stupid but when trying to upgrade my Amiga 2000 and add a SCSI CD-ROM I took out the side by side floppy drives without noting the cable rotation. When putting them back in I can't remember if they had the red sided floppy cables but I had to guess the orientation but they never seemed to work after that. I looked for a cheap replacement and eventually found two more A2000 systems but one was a 2000HD and the other a 2500 so I didn't have the heart to part them out.
- Soon I'll maybe regret trying to fix a Sun Tadpole 1. All I've really heard from the community is "don't". lol

De-soldering chips with only a cheap Radio Shack soldering pencil and nothing else. Broke traces and burned the hell out of an Apple II clone board and several others doing that. It is so nice having the right tools for the job these days!

I also sort of regret some of the "customizations" and bad repairs I did along time ago, but on the other hand I learned quite a bit from those experiences. No money for brand new overpriced Apple II parallel port card? No problem, I'll just build one of my own using spare TTL chips and the extra space on the motherboard! Hey, it worked with the Print Shop! Need it to work with the sync of an oddball monitor? No problem, add a few chips an rewire the motherboard! And I'm still trying to remember why I cut the data lines to Slot 7 and have wires running to it from elsewhere!

Also regret taking my TI-99/4a PEB apart (also a long time ago) and letting my bothers get a hold of the parts. The last time I saw the metal cage that is supposed to hold the cards in place, it was bent up and being used as a hat rack!

I kind of regret tearing up a CREI 680 training system someone had given to me assembled. Did a bunch of re-wiring and poor repairs on that too. But again I learned quite a bit, and did a bit of programing on it too.

More recently, I accidentally threw out a knob for an Atari 2600 paddle set because I thought it was a random knob from a printer or something. Later I'm looking a the paddles and notice there is a missing knob...

Plenty of other things I had to throw out over the years. But, you can't keep it all.

I regret tossing most of my old software boxes (kept the disks and manuals) around 2000 or so. This was before I went retro gaming.

Ah yes.. that's definitely one; although I look around today and see how much space those are taking still and wonder if it's worth it. Then there's the other thread about backing them all up and what hardware to spend the $$$ on. Which is my biggest complaint for a cheap arse like myself I know it takes time and money to make them and in reality for the cost of two or three of the games when they are new you can get most of them it's just the $1xx to see if it works is a bit painful.